IL40197A - Derivatives of 17-hydroxy-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid and the corresponding gamma-lactones and their preparation - Google Patents
Derivatives of 17-hydroxy-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid and the corresponding gamma-lactones and their preparationInfo
- Publication number
- IL40197A IL40197A IL40197A IL4019772A IL40197A IL 40197 A IL40197 A IL 40197A IL 40197 A IL40197 A IL 40197A IL 4019772 A IL4019772 A IL 4019772A IL 40197 A IL40197 A IL 40197A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- alkyl
- formula
- hydroxy
- oxo
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 4
- 125000000457 gamma-lactone group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 19
- 239000001257 hydrogen Substances 0.000 claims abstract 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 18
- 239000001301 oxygen Substances 0.000 claims abstract 18
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 17
- 150000001340 alkali metals Chemical class 0.000 claims abstract 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 13
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract 9
- 239000002253 acid Substances 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 8
- -1 alkali metal alkoxide Chemical class 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 239000002585 base Substances 0.000 claims abstract 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract 5
- 239000011707 mineral Substances 0.000 claims abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000012736 aqueous medium Substances 0.000 claims abstract 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract 3
- 229910021529 ammonia Inorganic materials 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000010306 acid treatment Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- UJVLDDZCTMKXJK-WNHSNXHDSA-N canrenone Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CCC(=O)C=C3C=C2)C)CC[C@@]11C)C[C@@]11CCC(=O)O1 UJVLDDZCTMKXJK-WNHSNXHDSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1368005 7-Carboxy steroids and related compounds G D SEARLE & CO 24 Aug 1972 [25 Aug 1971] 39401/72 Heading C2U Novel steroids have the formulµ wherein Z is H, alkali metal, alkaline earth metal/2, ammonium or alkyl; Z<SP>1</SP> is H, alkali metal, alkaline earth metal/2 or ammonium when Z is alkyl and is identical to Z when Z is H, alkali metal, alkaline-earth metal/2 or ammonium; the #<SP>1</SP> double bond is optional; the wavy line indicates the alternative α and # configurations; and X is oxygen, and it may also be sulphur when Z is alkyl and #<SP>1</SP> is absent in (Ia). They are prepared by (a) contacting 4α,7α - carbonyl - 5 - cyano - 17 - hydroxy - 3- oxo - 5#,17α - pregnane - 21 - carboxylic acid γ-lactone with an alkali metal alkoxide to afford a mixture of 7α and 7# compounds (Ia) wherein X is O, Z is alkyl and #<SP>1</SP> is absent, which may be separated by conventional procedures; (b) contacting an active acylating derivative of a compound (Ia) wherein X is O and Z is H, particularly a novel compound of the formula with an alkanol to give compounds (Ia) wherein X is O and Z is alkyl, the acylating derivatives (II) being prepared from the corresponding 7- carboxylic acids (Ia) and alkyl chloroformates in the presence of a tertiary amine; (c) dehydrogenating a compound (Ia) wherein X is O, Z is alkyl and #<SP>1</SP> is absent to give the corresponding #<SP>1,4</SP> compound, using, for example, 2,3-dichloro - 5,6 - dicyano - 1,4 - benzoquinone; (d) reacting a compound (Ia) wherein X is O and Z is alkyl or H with, respectively, one or two equivalents of a base, e.g. KOH, in an aqueous medium, to give the corresponding mono- or bis-metal salt (Ib) followed, when required, by brief exposure to a proton source to give the corresponding mono- or di-carboxylic acid (Ib); (e) hydrolysing under alkaline conditions a compound (Ia) wherein X is O and Z is alkyl followed by mineral acid treatment to give a compound (Ia) wherein X is O and Z is H; (f) contacting a starting material as defined in (b) above with an alkane thiol to give a compound (Ia) wherein X is S, Z is alkyl and #<SP>1</SP> is absent; (g) contacting a starting material as defined in (a) above with KOH in methanol followed by alkaline hydrolysis and subsequent mineral acid treatment to give a corresponding 7α compound (Ia) wherein X is O, Z is H and #<SP>1</SP> is absent; (h) contacting a compound (Ia) or (Ib) wherein X is O, Z is H or alkyl and Z<SP>1</SP> is H which contains at least one acid hydrogen with an appropriate quantity of a base in an aqueous medium to give a corresponding mono- or bis-metal salt of a compound (Ia) or (Ib); or (i) contacting a compound (Ia) wherein X is O and Z is H or a compound (Ib) wherein X is O, Z is H or alkyl and Z<SP>1</SP> is H with excess ammonia to give a corresponding ammonium salt. 4α,7α - Carbonyl - 5 - cyano - 17 - hydroxy - 3- oxo - 5#,17α - pregnane - 21 - carboxylic acid γ-lactone is prepared by heating 17-hydroxy-3- oxo - 17α - pregna - 4,6 - diene - 21 - carboxylic acid γ-lactone with an alkali metal cyanide under slightly basic conditions in a solvent followed by heating the resulting 7α,4-aminomethylidyne - 5 - cyano - 17 - hydroxy - 3 - oxo- 5#,17α - pregnane - 21 - carboxylic acid γ- lactone with very dilute aqueous mineral acid (see Specification 1,368,006). The novel steroids of the Formulµ (Ia) and (Ib) are diuretic and blood pressure-lowering agents. They may be made up into pharmaceutical compositions with suitable carriers.
[GB1368005A]
Claims (1)
1. WHAT WE CLAIM IS : 1. A compound of the general formula wherein Z is hydrogen, alkali metal, alkaline-earth metal/2, ammonium or alkyl; Z' la hydrogen, alkali metal, alkaline-earth metal/2 or ammonium when Z is alkyl; Z* is Identical to Z when Z is hydrogen, alkali metal, alkaline—earth metal/2 or ammonium; the dotted lino indicates the optional presence of a unsaturated llnkago; the wavy lino indicates the alternative a and β configurations; and X lo oxygen, with the proviso that when Z io alkyl and the 1,2-llnkago is saturated, X in formula (la) can aleo be sulfur,. 2. 17-Hydroxy-3-oxo-17a-pregn- -ene-7a, 21- dicarboxylic acid -lactone. >. 3. A compound of the general formula wherein Z" is alkali metal or alkaline-earth metal/2; and the dotted line indicates the optional presence of a Δ1 unsaturated linkage. 4. A compound of the general formula wherein Z" is alkali metal or alkaline-earth metal/2. 5. 7a-Ethoxycarboriyl-17-hydroxy-3-oxo-17o pregn- -ene-21-carboxylic acid 7-lactone. 6. 17-Hydroxy-7a-methoxycarbonyl-5-oxo-17a- pregn- -ene-21-carboxylic acid 7-lactone. 7. 17-Hydroxy-7c-isopropoxycarbonyl-5-oxo-17ct- pregn- -ene-21-carboxylic acid 7-lactone. 8. Potassium 17-hydroxy-7a-methoxycarbonyl-2- oxo-17o pregn- -ene-21-carboxylate. 9. Potassium 17-hydroxy-7a-isopropoxycarbonyl- oxo-17a-pregn- -ene-21-carbox late. 10. Potassium 7a-ethoxycarbonyl-17-hydroxy-5- oxo-17ct-pregn- -ene-21-carboxylate. 40197-2 | . 11. A process for the preparation of a compound of the general formula gCOOZ ' wherein Z la hydrogen, alkali metal, alkaline-earth metal/2 , ammonium or alkyl; Z* i3 hydrogen, alkali metal, alkaline-earth metal/2 or ammonium when Ζ is alkyl; Ζ' is identical to Z when Z is hydrogen, alkali metal, alkaline-earth metal/2 or ammonium; the dotted line indicates the optional presence of a unsaturated linkage; the wavy line indicates the alternative a and p configurations; and X is oxygen, with the proviso that when Z is alkyl and the 1,2-linkage is saturated, X in formula (la) can also "be sulfur, which comprises a process eoloctcd iron th group consisting of: (a) contacting a,7a-carbonyl-5-cyano-17-hydroxy- 3-oxo-5 ,17a-pregnane-21-carboxylic acid /-lactone with an alkali metal alkoxide, to afford a mixture of the corresponding 7a and 7β compounds of formula (la) wherein X is oxygen, Z is alkyl and the 1,2-linkage is saturated, followed by isolation of the desired 7 or 7β isomer; 40197-2 (b) contacting an active acylating derivative of a compound of formula (la) wherein X is oxygen and Z is hydrogen with an alkanol, to afford the corresponding compound of formula (la) wherein X is oxygen and Z is alkyl; (c) dehydrogenation of a compound of formula (la) wherein X is oxygen, Z is alkyl and the 1,2-linkage is saturated, to afford the corresponding compound of formula (la) wherein X is oxygen, Z is alkyl and the 1,2-linkage is unsaturated; (d) contacting a compound of formula (la) wherein X is oxygen and Z is alkyl or hydrogen with, respectively, one or two equivalents of an appropriate base, in an aqueous medium, to afford the corresponding mono- or bis- (alkali metal) or (alkaline-earth metal/2) salt of formula (lb); followed by, if desired, brief exposure to a proton source, to afford the corresponding mono- or dicarboxylic acid of formula (lb); (e) alkaline hydrolysis of a compound of formula (la) wherein X is oxygen and Z is alkyl, followed by treatment with mineral acid to afford the corresponding compound of formula (la) wherein X is oxygen and Z is hydrogen; (f) contacting an active acylating derivative of a compound of formula (la) wherein X is oxygen, Z is hydrogen and the 1,2-linkage is saturated with an alkane-thiol, to afford the corresponding compound of formula (la) wherein X is sulfur, Z is alkyl and the 1,2-linkage is saturated; (g) contacting a, 7a-carbonyl-5-cyano-17-hydroxy-3-oxo-5P, 17cc-pregnane-21-carboxylic acid 7-lactone with potassium hydroxide in methanol, followed by alkaline hydrolysis and subsequent treatment with mineral acid to afford the corresponding a compound of formula (la) wherein X is oxygen, Z is hydrogen and the 1, 2-linkage is saturated (h) contacting a compound of formula (la) or (lb) wherein X is oxygen, Z is hydrogen or alkyl and Z' is hydrogen, Z and Z1 being selected so that the molecule contains at least one acid hydrogen, with a quantity of an appropriate base equivalent to the amount of acid hydrogen present, in an aqueous medium, to afford the corresponding mono- or bis- (alkali metal) or (alkaline- earth metal/2 ) salt of formula (la) or (lb); and (i) contacting a compound of formula (la)- wherein X is oxygen and Z is hydrogen or a compound of formula (lb) wherein X is oxygen, Z is hydrogen or alkyl and Z' is hydrogen, with excess ammonia, to afford the corresponding compound of formula (la) wherein X is oxygen and Z is ammonium or of (lb) wherein X is oxygen, Z is ammonium or alkyl and Z1 is ammonium, respectively. 12. . A process according to Claim 11(b) wherein the active acylatlng intermediate is the anhydride of 17-hydroxy-2-oxo-17a-pregn- -ene-7a, 21-dicarboxylic acid 7-lactone with an alkoxyformic acid. 40197-2 13· A process according to Claim 11(c) wherein the dehydrogenation is effected by use of 2, 5-dichloro-5,6-dicyano-l, -benzoquinone. 14. A process according to Claim 11(d) wherein the base is potassium hydroxide. 15. A process for the preparation of 17-hydroxy-7a-methoxycarbonyl-5-oxo-17ct-pregn- -ene-21-carboxylic acid 7-lactone which comprises contacting a,7a-carbonyl-5-cyano-17-hydroxy-j5-o o-5β,17α-pre nane-21-carboxylic acid 7-lactone with an alkali metal methoxide, followed by isolation of the desired 7a isomer. 16. A process for the preparation of a 7<*-alkoxycarbonyl-17-hydroxy-3-oxo-17a-pregn- -ene-21-car-boxylic acid y-lactone wherein the alkoxy group is ethoxy, methoxy or isopropoxy, which comprises contacting ethanol, methanol or 2-propanol, respectively, with the mixed anhydride of an alkoxyformic acid and 17-hydroxy-3-oxo-17a-pregn- -ene-7a>21-dicarboxylic acid 7-lactone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17492271A | 1971-08-25 | 1971-08-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40197A0 IL40197A0 (en) | 1972-10-29 |
| IL40197A true IL40197A (en) | 1976-05-31 |
Family
ID=22638078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40197A IL40197A (en) | 1971-08-25 | 1972-08-24 | Derivatives of 17-hydroxy-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid and the corresponding gamma-lactones and their preparation |
Country Status (21)
| Country | Link |
|---|---|
| JP (2) | JPS5839840B2 (en) |
| AT (1) | AT323907B (en) |
| AU (1) | AU475957B2 (en) |
| BE (1) | BE787940A (en) |
| CA (1) | CA970361A (en) |
| CH (2) | CH601350A5 (en) |
| DE (1) | DE2241680C2 (en) |
| DK (1) | DK133954B (en) |
| ES (2) | ES406044A1 (en) |
| FI (1) | FI50429C (en) |
| FR (1) | FR2150852B1 (en) |
| GB (1) | GB1368005A (en) |
| IE (1) | IE36653B1 (en) |
| IL (1) | IL40197A (en) |
| KE (1) | KE2813A (en) |
| MY (1) | MY7800121A (en) |
| NL (1) | NL176569C (en) |
| NO (1) | NO134990C (en) |
| PH (1) | PH9271A (en) |
| SE (2) | SE380533B (en) |
| ZA (1) | ZA725839B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069219A (en) * | 1976-12-27 | 1978-01-17 | G. D. Searle & Co. | 7ξ-(Alkoxycarbonyl)-6ξ-alkyl/halo-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactones and corresponding 21-carboxylic acids, their salts, and esters |
| FR2496669A1 (en) * | 1980-12-23 | 1982-06-25 | Roussel Uclaf | NOVEL STEROID 3-KETO4 OR 1-4 SUBSTITUTED DERIVATIVES IN POSITION 7, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS MEDICAMENTS |
| DE3111951A1 (en) * | 1981-03-23 | 1982-09-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 7 (ALPHA) -ALKOXYCARBONYL-15SS-METHYLENE-4-ANDROSTENE, METHOD FOR THE PRODUCTION AND USE THEREOF AS A MEDICINAL PRODUCT |
| JPS57169230A (en) * | 1981-04-10 | 1982-10-18 | Matsushita Electric Ind Co Ltd | Oil-immersed plastic ilm capacitor |
| US5296318A (en) * | 1993-03-05 | 1994-03-22 | Bell Communications Research, Inc. | Rechargeable lithium intercalation battery with hybrid polymeric electrolyte |
| JP2008512439A (en) * | 2004-09-09 | 2008-04-24 | ファルマシア コーポレーション | Process for preparing 7α-alkoxycarbonyl substituted steroids |
-
0
- BE BE787940D patent/BE787940A/en not_active IP Right Cessation
-
1972
- 1972-08-21 AU AU45787/72A patent/AU475957B2/en not_active Expired
- 1972-08-23 ES ES406044A patent/ES406044A1/en not_active Expired
- 1972-08-24 ZA ZA725839A patent/ZA725839B/en unknown
- 1972-08-24 CA CA150,118A patent/CA970361A/en not_active Expired
- 1972-08-24 FR FR7230235A patent/FR2150852B1/fr not_active Expired
- 1972-08-24 NL NLAANVRAGE7211559,A patent/NL176569C/en not_active IP Right Cessation
- 1972-08-24 IL IL40197A patent/IL40197A/en unknown
- 1972-08-24 DE DE2241680A patent/DE2241680C2/en not_active Expired
- 1972-08-24 NO NO3032/72A patent/NO134990C/no unknown
- 1972-08-24 PH PH13830*UA patent/PH9271A/en unknown
- 1972-08-24 GB GB3940172A patent/GB1368005A/en not_active Expired
- 1972-08-24 SE SE7210976A patent/SE380533B/en unknown
- 1972-08-24 IE IE1160/72A patent/IE36653B1/en unknown
- 1972-08-24 DK DK420472AA patent/DK133954B/en not_active IP Right Cessation
- 1972-08-24 AT AT733172A patent/AT323907B/en not_active IP Right Cessation
- 1972-08-24 FI FI722353A patent/FI50429C/en active
- 1972-08-25 CH CH1262572A patent/CH601350A5/xx not_active IP Right Cessation
- 1972-08-25 JP JP47085217A patent/JPS5839840B2/en not_active Expired
-
1974
- 1974-12-04 SE SE7415187A patent/SE404024B/en unknown
-
1975
- 1975-02-28 ES ES435189A patent/ES435189A1/en not_active Expired
-
1977
- 1977-03-25 CH CH383477A patent/CH603689A5/xx not_active IP Right Cessation
-
1978
- 1978-01-19 KE KE2813A patent/KE2813A/en unknown
- 1978-12-30 MY MY121/78A patent/MY7800121A/en unknown
-
1982
- 1982-10-29 JP JP57190666A patent/JPS5890598A/en active Granted
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